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Deciphering the Origin of Stereoinduction in Cooperative Asymmetric Catalysis Involving Pd(II) and a Chiral Bronsted Acid

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Title Deciphering the Origin of Stereoinduction in Cooperative Asymmetric Catalysis Involving Pd(II) and a Chiral Bronsted Acid
 
Creator JINDAL, G
SUNOJ, RB
 
Subject C-H ACTIVATION
MECHANISTIC INSIGHTS
SPIROCYCLIC RINGS
GAMMA-LACTAMS
METAL
ORGANOCATALYSIS
CYCLOADDITION
ARYLATION
STRATEGY
CARBENES
 
Description The density functional (M06) computations on a cooperative multicatalytic reaction involving palladium acetate and a chiral Bronsted acid in the conversion of an indenyl cyclobutanol to spirocyclic indene bearing a quaternary carbon ring junction are reported. A chiral Pd-bis-phosphate is identified as the active catalyst in the enantioselective ring expansion as compared to alternative possibilities wherein the chiral phosphate/phosphoric acid is in the outer sphere of palladium. The enantiocontrolling transition state exhibited more effective C-H...pi interactions, lower distortion of the catalyst, and an orthogonal orientation of the bulky phosphate ligands.
 
Publisher AMER CHEMICAL SOC
 
Date 2016-01-15T06:16:27Z
2016-01-15T06:16:27Z
2015
 
Type Article
 
Identifier ORGANIC LETTERS, 17(12)2874-2877
1523-7060
1523-7052
http://dx.doi.org/10.1021/acs.orglett.5b00860
http://dspace.library.iitb.ac.in/jspui/handle/100/17909
 
Language en